1. Field of the Invention
The present invention deals with the composition, and application of novel quaternary polymeric compounds, as softening, anti-tangle, and conditioning agents for use in personal care, textile and related applications. The properties of these novel quaternary polymeric compounds which makes them well suited for these applications is the fact that they are substantive to fibers, hair and skin and also very mild to the skin and eyes. Additionally, unlike many polymers used in the market which are the result of a free radical process, the compounds of this invention are not free radical based, rather are based upon more traditional fatty chemistry, consequently the products are easier to control and give outstanding batch to batch consistency. This consistency is critical to many high performance personal care products.
2. Description of the Art Practices
Standard quaternary compounds are prepared by quaternization of a tertiary amine with such agents as benzyl chloride or di-methyl sulfate or di-ethyl sulfate or methyl chloride. These materials are relatively inexpensive but offer several key disadvantages. These include yellowing of fabrics, a tendency to build-up upon repeated treatment, and variability in hand (i.e. softness and feel). Standard softeners used are selected from the following classes:
Class #1. Alkyl Imidazoline Quaternary Compounds made from the quaternization of an imidazoline made by reacting diethylenetriamine, and a high molecular weight fatty acid such as stearic acid. The standard quaternizating agents are di-ethyl sulfate, or methyl chloride, or di-methyl sulfate, or methyl chloride or benzyl chloride. PA1 Class #2. Alkyl or dialkyl tertiary amines quaternized with benzyl chloride or di-ethyl sulfate or methyl chloride or di-methyl sulfate PA1 Class #3. Quaternary compounds of ethoxylated, propoxylated or nonalkoxylated amido amines derived from the reaction of a high molecular weight fatty acid like stearic acid and a polyamine like diethylene triamine. The standard quaternizating agents are di-ethyl sulfate or di-methyl sulfate or methyl chloride or benzyl chloride. PA1 Class #4. Amido amine salts derived from partially acid neutralized amines. PA1 CH.sub.3 --(CH.sub.2).sub.e --CH(CH.sub.3)--(CH.sub.2).sub.f --; PA1 CH.sub.3 --(CH.sub.2).sub.b --O--R--.sup.1 (CH.sub.2).sub.3 --; PA1 CH.sub.3 --(CH.sub.2).sub.d --CH(CH.sub.3 13 (CH.sub.e --O--R.sup.1 --(CH.sub.2).sub.3 --; and ##STR5## R.sup.1 is EQU --(CH.sub.2 CH.sub.2 --O).sub.x --(CH.sub.2 CH(CH.sub.3)--O).sub.y --(CH.sub.2 CH.sub.2 --O).sub.z --; PA1 x y and z are independently integers from 0 to 20; PA1 b,c,d,e are each independently integers from 5 to 20; PA1 m and n are each independently integers from 4 to 20. PA1 CH.sub.3 --(CH.sub.2).sub.e --CH(CH.sub.3)--(CH.sub.2).sub.f --; PA1 CH.sub.3 --(CH.sub.2).sub.b --O--R.sup.1 --(CH.sub.2).sub.3 --; PA1 CH.sub.3 --(CH.sub.2).sub.d --CH(CH.sub.3)--(CH.sub.2).sub.e --O--R.sup.1 --(CH.sub.2).sub.3 --and ##STR9## R.sub.1 is EQU --(CH.sub.2 CH.sub.2 O).sub.x --(CH.sub.2 CH(CH.sub.3 --O).sub.y --(CH.sub.2 CH.sub.2 --O).sub.z --; PA1 x y and z are independently integers from 0 to 20; PA1 b,c,d,e are independently integers from 5 to 20; PA1 m and n are independently integers from 4 to 20; PA1 CH.sub.3 --(CH.sub.2).sub.e --CH(CH.sub.3)--(CH.sub.2).sub.f --; PA1 CH.sub.3 --(CH.sub.2).sub.b --O--R.sup.1 --(CH.sub.2).sub.3 --; PA1 CH.sub.3 --(CH.sub.2).sub.d --CH(CH.sub.3)--(CH.sub.2).sub.e --O--R.sup.1 --(CH.sub.2).sub.3 --; and ##STR14## R.sup.1 is EQU --(CH.sub.2 CH.sub.2 --O).sub.x --(CH.sub.2 CH(CH.sub.3)--O).sub.y --(CH.sub.2 CH.sub.2 --O).sub.z --; PA1 x y and z are independently integers from 0 to 20; PA1 b, c, d, e are independently integers from 5 to 20; PA1 m and n are independently integers from 4 to 20; PA1 a is an integer from 2 to 2,000; PA1 Q is an anionic counter ion needed for charge balance and is selected from chlorine, bromine, sulfate, and phosphate.
It is known that under certain catalytic conditions, epichlorohydrin reacts with certain alcohols to give an intermediate which can be used to react with tertiary amines to quaternary compounds. U.S. Pat. No. 3,445,440 to Susi (May 1969) and U.S. Pat. No. 3,517,045 to Susi (June 1970) teaches the use of chlorohydroxypropyl ether to alkylate specific tertiary amines which are the reaction product of a primary fatty amine and ethylene or propylene oxide to give compounds conforming to the following structure; ##STR3##
The Susi compounds are used as antistatic agents in polymeric compositions such as polyolefin. The antistatic properties of these compounds are achieved by the minimization of static charges on the polymer surface. These antistatic materials are incorporated into the polymer melt and are effective by virtue of their insolubility in the molten polymer. The quaternary compounds migrate to the polymer surface and are effective antistatic agents.
U.S. Pat. No. 4,144,122 to Emanuelsson issued Mar. 13, 1979 teaches that tallow alcohol and certain other higher molecular weight alcohols and their alkoxylates can be reacted with epichlorohydrin, then subsequently with tertiary amines to give compounds suitable for paper debonding.
U.S. Pat. No. 4,215,064 to Lindemann et al issued July 29, 1980 teaches that phosphobetaines can be prepared by the reaction of a phosphate or phosphite salt with epichlorohydrin under aqueous conditions. U.S. Pat. No. 4,283,541 to O'Lenick, et al, issued Aug. 11, 1981 teaches the process for the preparation of the phosphobetaines described in Lindemann (U.S. Pat. No. 4,215,064). None of these patents teach the compounds of the present invention.
Polyvinylpyrrolidone (pvp), a well known material of commerce, has been prepared by the free radical polymerization of vinyl pyrrolidone using standard free radical initiators. Polyvinylpyrrolidone (pvp) polymers are nonionic in nature, form resinous films and as will become apparent from this disclosure, do not possess the hydrophobic fatty portion of the molecule, which comes from the amino amine raw material.
The reaction of primary amines has been disclosed with butyrolactone in various publications, including U.S. Pat. No. 4,423,040 issued to Rajadhyaksha Dec. 27, 1983, which teaches that 1-substituted azacyclohexan-2-ones can be prepared and used as physiologically active agents. Related patents to Rajadyaksha include U.S. Pat. Nos. 4,525,199; 4,461,638; 4,444,762; 4,562,075; 4,316,893; 4,122,170; 4,405,616; and 4,415,563. None of these referenced patents teach the compounds of the present invention.